Decyne

The higher homologues of propyne, e.g. 1-decyne, can be obtained in a similar way. Starting from 1-butyne and its homologues, alkylation with alkyl halides leads to 1-alkynes with a branched substituent. 

When 1 2 dibromodecane was treated with potassium hydroxide m aqueous ethanol it yielded a mixture of three isomenc compounds of molecular formula CioHi9Br Each of these compounds was converted to 1 decyne on reaction with sodium amide m dimethyl sulfoxide Men tify these three compounds... 

C9H20 4.4-DIMETHYL- -246.853 8.7750E-01 6.2463E-05 21.00 443 C10H18 1-DECYNE 37.488 7.0119E-01 5.7516E-05 252.21... 

Primary and secondary amines, when added to fluorine-containing alkynes, yield secondary or tertiary fluoroalkylenamines For example, 1-hydroperfluoro 1 decyne reacts with secondary amines in a variety of solvents at 5 °C to give A / f-dialkyl-Ul-dihydroperfluoro 1 decenamines as products The configuration of the double bond is probably E [9]... 

How would you synthesize stearolic acid (Problem 27.19) from 1-decyne and l-chIoro-7-iodoheptane ... 

The boronic acid ester B was synthesized by transesterification of the corresponding pinacolester A with (lR,2R)-l,2-dicyclohexyl-l,2-dihydroxyethane. Stereoselective chlorination of B was carried out with (dichloromethyl) lithium and zinc chloride. Reaction of the obtained chloroboronic ester C with lithio 1-decyne followed by oxidation of the intermediate D with alkaline hydrogen peroxide afforded the propargylic alcohol E. Treatment with acid to saponify the tert-butyl ester moiety and to achieve ring closure, produced lactone F. Finally, Lindlar-hydrogenation provided japonilure 70 in an excellent yield and high enantiomeric purity. 

Shin and Ogasawara reported a new total synthesis of carazostatin (247) from N-carbethoxy-2-iodoaniline (700) and 1-decyne involving two aromatic annulation... 

A. (E)-l-Deaenyidiisobutylalane. An oven-dried, 300-mL, two-necked, round-bottomed flask equipped with a magnetic stirring bar, a rubber septum inlet, and an outlet connected to a mercury bubbler is flushed with nitrogen, immersed in a water bath kept at room temperature, and charged with 22.6 ml (125 mmol) of 1-decyne (Note 1) and 80 mL of hexane (Note 2). To this flask is added dropwise, with stirring, 22,3 mL (125 mmol) of diisobutylaluminum... 

The submitters used 1-decyne from Farchan Laboratories, Inc., without further purification. The checkers used the material purchased from Aldrich Chemical Company, Inc. and Tokyo Kasei Kogyo Company. 

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